Cyclopolymerization of Diallylamines

Interest in the polymerization of diallylamines and various substituted diallylamines, including triallylamine, has been stimulated by the successful industrial development of flocculants [l] and “Sirotherm” ion-exchange resins [2] based on these polymer systerns. The polymers also have potential applications in such diverse areas as fiber [3] and paper [4] technology, and in the sequestration of heavy-metal cations [5]. The free radical induced polymerization diallylamines (1), like that of other 1,6-dienes (7), has been shown to proceed by a series of alternate intra-intermolecular additions with the formation of chains comprising pyrrolidine (5) and/or piper-idine (6) derived moieties (Scheme 1) [6]. This process of polymerization via a series of alternate intra-intermolecular additions is known as cyclopolymerization [7]. Polymers derived from diallylamines are not only of commercial significance, but are also of scientific interest as their polymerization mechanisms raise a number of points of fundamental importance to polymer chemistry and to free radical chemistry in general.